New Dawn
by BlizzardNova
Summary: Tears streamed down her face when she thought of his name, leaving streaks of warm tears down her cheeks. "I-I can't be alone anymore...I can't-", Her sobs were finally silenced with a warm embrace and comfort just flooded her entire being as she melted into it. "You will never be alone again, you hear me? I'll always be here for you, Dawn." (CavalierShipping) (Dawn in Alola)
1. Chapter 1- Empty

**(A/N): So this story is a 'rewrite' of my previous story known as 'Chasing Daydreams' posted like last year or something, I've since deleted it (Only had like 2 chapters anyways) and am attempting to do a better idea of it in this more updated version. Just to be clear this story is CavalierShipping (GaryXDawn) with a likely inclusion of Amourshipping, I also have a Pearlshipping story planned sometime in the future but for now I have this idea that I must do with this pairing. Rating is T for now, but I am likely going to bump that up to M in future chapters if I decide to take that route, so just be wary of that. The story is essentially going to be what I would think it would be like if Dawn was to travel to the Alola region. Honestly there is not enough CavalierShipping Fanfiction out there, so please recommend me some if you find any!**

 **CONTAINS SPOILERS FOR POKEMON SUN AND MOON**

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Sun peered through the small window on the side of the bedroom, making the soft and pink carpet glow with a tinge of brightness. The faint breeze outside rippled around the house and made a small yet peaceful noise that most would find comforting, however nothing but a sigh emerged from the young woman lying on her bed just staring at the ceiling, the beauty of the sunset outside not enough to pry her eyes from her deep thoughts.

Her head sinks back into the big plush pillow resting behind her. Her blue hair splashes around her head, draping around the bed as it glimmers in a brilliant calm radiance in the rays of the sunset from the window beside the blue haired young woman.

Dawn, that was her name and she certainly could fit that description. Although her face looked a bit pale and washed out at the moment, her eyes were still twinkling with their deep blue azure that when you look at them you can't help but feel like you are deep under an ocean with little bubbles of light that just glimmer and radiate everything they touch. Truly the years had done her good, now aged eighteen she really looked mostly all grown up. Since she was always in the spotlight being a coordinator, maintaining her body and face has always been an important factor and her beauty certainly did not go unnoticed, especially among the male crowd. On top of showing off the beauty in her Pokémon she would often be offered jobs where she would model herself as well.

Things seemed like they were all fine and dandy in Dawn's life, yet something was still troubling her…Something she never really experienced all her life… Something called love. Ever since she was just a ten-year old girl, she developed a small crush on her traveling companion… Ash Ketchum. Dawn would always cherish the moments she spent with Ash and Brock during this time, however their adventures through Sinnoh were a bit short-lived unfortunately. After the short years had passed, Ash was off to another region called Unova. Dawn decided to visit him there actually, as she had business with Champion Cynthia anyways. While there, she only felt her feelings for him blossom more and more, watching how courageous and kind of person he was, she could only dream of being that inspiring. While she didn't outright profess her feelings towards him, it was clear at least to her that he didn't feel the same.

It's been at least three years since she visited him in Unova and in this time Ash had gone through the Kalos region for another two, and now he was going to be in the Alola region. She knew this because of something that really caught her attention on the television she was just watching, which was actually the cause of this sudden burst of sadness.

Dawn would often watch Ash on the television when he would do any major sorts of battles, not in a stalker type of way, more of a friendly 'love stricken' way. As she watched she would always be inspired by his unique battle style and always try to blend those techniques into contests. Ash had lost the Kalos league much to Dawn's dismay but that wasn't what bothered her. What bothered her was the girl traveling with him… Serena… Or so she heard that was her name.

While Dawn wasn't the jealous type, but it was clear that this girl… Serena was in love with Ash. She had even heard rumors of her coming along with Ash to the Alola region which would most definitely solidify that relationship and leave Dawn alone with nothing.

Alone…That's what she was right now…Alone…

She felt her eyes mist up a little and she sat up and curled her legs into her chest, her head drooping down on top of her knees.

It was a silly thought, the idea of her and Ash together. Why would he want someone like herself… When he could have any girl he wanted.

These thoughts weighed on her mind and the small mist from her eyes flowed into streams of tears, her head still buried beneath her knees as she began to slowly weep.

It wasn't long before something touched the bottom of her foot, and in a sudden act of surprise, Dawn immediately looks up as her tears are momentarily halted. That some 'thing' that had touched her was in fact none other than her starter Pokémon and most trusted partner, Piplup.

Clearly distraught and worried for it's trainer's well-being as it looks into Dawn's eyes with it's own with empathy. Dawn sniffles a bit and feels her nose twitch as she outstretched her hand and pats Piplup on the head reassuringly.

"I'm fine Piplup, no need to worry." She whispered as a small tear leaked out of her left eye and dripped down her chin.

The door to Dawn's room suddenly burst open and revealed Johanna, Dawn's mother, with a face of business plastered over it.

"Alright Dawn, this has gone on long enough." Johanna says sternly as she begins walking in Dawn's room uninvited.

Dawn immediately sits up straight and subtly wipes away the newest tear formed from her eye and forces out a smile as she looks at her mom innocently. "Oh hi mom… Can I help you?" Dawn speaks shakily, trying so hard to hide the sadness behind her words.

"Dawn, please." Johanna lets out a little chuckle, "I've raised you from birth, and I think I can tell when my daughter is upset about something, no need to hide it." Johanna continues as she takes a seat next to Dawn on the bed. "I also know that she's very good at bottling up her emotions and not talking about them." She lets out a smile as she places her hand gently on the back of Dawn to comfort her.

"It's fine mom… It's not really a big deal…" Dawn brushes the subject off as she turns her body away from Johanna unknowingly.

Johanna shook her head and laughed a little, her hand still placed on Dawn's back, "If it's not a big deal then why have you locked yourself in your room for a week?" Dawn turned back to face Johanna and opened her mouth to speak, but no words were uttered. "Come to think of it, you rarely come to visit me, except when you are upset about something." Johanna continued as she smiled at Dawn, a hint of teasing and compassion was embedded in her voice. At this point Dawn just gave up trying to hide it, her mother was far too good at reading her that it was pointless.

"Alright… You caught me…I've just been thinking a lot and it's been upsetting me, that's all." Dawn spoke honestly.

"Thinking about what exactly?" Johanna pried a bit, in hopes of picking up on something so that she could help her daughter through these 'flash depressions'.

"The past." Dawn says directly as she turns back to face the wall blankly, her hands once again wrapping back around her knees and holding them close to her chest.

The older bluenette finally realized she wasn't going to get anywhere with Dawn at this stage, so she just sighed and stood up from the bed. "Well I can see you still need some time." She sighed in defeat.

"Don't forget to pay attention to your Pokémon, Dawn. They say trainers and Pokémon's emotions are connected and I wouldn't be surprised if all your Pokemon are feeling the same as you are now." Johanna concluded as she stepped out of the room to give Dawn some space.

The words seemed to stick with Dawn a little, because as soon as Johanna left the room Dawn turned her attention to Piplup who looked about ready to cry, with his flippers covering his eyes as he whimpered in sympathy for his trainer.

"Oh no…Piplup… What have I been doing?" Dawn quivered as she grabbed Piplup and pulled him for a tight hug. The penguin Pokémon snuggled up in the hug with Dawn as the tears from both began to stop.

"Piplup I'm sorry, I shouldn't have ignored you. I know you're just worried and I appreciate that very much." Dawn closed her eyes and finally released Piplup from the hug.

"Pip! Pip-Pip Lup!" (About time you actually started talking to me again!) Piplup chirped out with a more happy and mellowed tone, much to Dawn's relief.

Taking a quick look at the window beside her, she sighed and creaked out a small genuine smile. "Hey, Piplup." Dawn called out to the happily chattering Pokémon on her bed, who was apparently didn't realize he was rambling to himself about who knows what. The penguin Pokémon looked back up to Dawn attentively with a confused look.

"I think I'm gonna take a little walk, it looks so nice out and I could use the fresh air, want to come?" She beckons as she begins to stand from her bed. Piplup looked at the window and then looked at Dawn's pillow. Flopping himself on the pillow it was clear he was more interested in sleep than going on this walk Dawn had planned.

"Alright, suit yourself." She covered her mouth as she let out a small giggle.

Walking up the mirror she looks at herself wearing a simple black tee and long jeans, her hair completely down and straight. Shrugging at herself and thinking back to when she was just a ten-year old girl and how obsessed she would have been with picking her outfit and styling her hair. It was so long ago and she had matured a lot from then. Just as she was about to step out her door, she could not help but at least put some makeup on, completely contradicting her earlier thoughts. Not that she cared, Dawn wasn't the type of person to compromise her values, and if she wanted to look pretty for herself, then she was darn well going to do just that.

Piplup stared at her, sitting atop the pillow and rolled his eyes. "Lup Piplup." (Some things never change.)

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 **Well it's a bit short but that's Chapter 1, Tried to just get all the introduction blah out of the way so the real story can really begin, let me know what you think with a review!**


	2. Chapter 2- Unexpected Rendezvous

**(A/N): Chapter 2 is up! A little bit longer than Chapter 1 at least. Thanks so much for all the favorites and follows, it means a lot to me!**

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Dawn took her first steps outside for what seemed like eternity, all this time bottled up in her room was unhealthy and it was time to get over this whole ordeal as her mom said earlier. Dawn did feel a bit bad at brushing off her mother like that, but she decided it was best not to dwell on that and just try and enjoy herself.

Faint breezes trickle up upon her face and cause her hair to wander about in random strands. Dawn chuckled a little to herself, having her old hat on right now would probably help prevent the messiness the world likes to throw at her. She sighed and combed her hair with her fingers as she walked, not like there was anyone to impress anyways. This was Twin-leaf town, and most of the modeling and coordinator business was done in bigger cities like Jubilife.

It was a few minutes before Dawn even realized that she needed some idea of where she was going to walk to. Deciding to just relax at the lake, she begins walking left to Lake Valor.

The fresh scent of the pine trees left a small genuine smile upon Dawn's face, ' _this walk was going to bring something good after all'_ , she thought to herself.

Lake Verity was certainly brilliant at this time of day, the reflecting light twinkled off of the small rippling waves. Dawn took in the view and was appreciating it rather than reflecting on what she was thinking about earlier.

It would all seem well, until something in the trees above her began to shake. At first it didn't worry her, but then she realized, she had no Pokemon on her.

Backing up from the shaking tree slowly she hoped that she could just get away from whatever 'thing' was making that noise. The soft patter of the gravely dirt beneath her was certainly not helping her back away quietly. Despite this noise it looked like she was going to get away until she unfortunately happened to step on a small twig and snapped it in two. The sound reverberated just enough to cause the creature in the trees to emerge. It was in fact a couple of Ariados, spider-like Pokemon. After feeling a bit of deja vu from her first adventure, she began to back away at a more rapid pace, no way she was going to be dealing with a bunch of these spiders without any Pokemon.

The Ariados did not look so pleased to see this young woman in their nesting area, one of them hissed at her and shot a sticky string-shot of web at her feet.

"Eep!" Dawn squealed as she quickly lifted her feet backwards to avoid the incoming shot, her eyes dilated in terror as she darted as far away as she possibly could from that tree.

' _So much for a peaceful walk…'_ She thought with a hint of annoyance in her mind.

Dawn kept running for what seemed like forever, although she knew these forest's well, she should have known better than to go walking around at this season with the Ariados crawling around without any Pokemon to protect her.

She was so deep in thought that she wasn't really even looking where she was going really, and before she knew it she hit something and yelped a little in response to the surprise.

Her eyes were still a bit hazy from the hit, it must have been a tree or something she thought to herself, but in fact it wasn't a tree. As her vision began to focus she noticed that it was… a _person…_

"Oh my gosh, I am so sorry! I was running from some Pokemon and I-I…" Dawn flustered, still not meeting the eyes of this stranger in guilt of what she just did.

"Hey now, you're fine, accidents happen." The voice replied, it was quite deep and masculine sounding and the type of voice that just melts easily on your ears and is pleasing to listen to.

Dawn couldn't help but look down at her feet in embarrassment, her hair now quite a mess from all the running was draped down over her face, so that she couldn't really get a good look at this stranger and he couldn't really look at her either.

"I-uh…Sorry again about that." Dawn stuttered as she twiddled her fingers awkwardly.

"Heh, You're fine." He repeated again, almost sounding like he was going to laugh at how awkward she was right now.

Dawn finally looked up, adjusting her silky blue hair off her face, she pushed it back and around her ears so her face was visible entirely. Her blue eyes twinkled as she looked straight into the eyes of this 'stranger', who in fact was no stranger to Dawn at all.

As she quickly scanned his face, immediately she identified him as none other than the grandson of her favorite poet in the Kanto region. The man in front of her was Gary Oak, it had been about 7 years since she had seen him last on her first journey through Sinnoh… When she was still with Brock and Ash.

Dawn didn't know what to say honestly, as she looked at him more and more she was getting lost in his face, she couldn't lie… He was certainly extremely attractive. His hair was as spiky as it was years ago, his face was defined with a chiseled jaw, and his body was quite well built which left Dawn's eyes to wander a bit. She didn't linger long though as she realized she was staring him down when he probably wouldn't even recognize her.

"H-hi… My name's-"

"Dawn." He finished before she could. Gary's eyes were fixated upon Dawn, he wasn't as subtle in the staring, he was too mesmerized by Dawn to even care at this point. It had only been seconds but the world around him seemed to blur out and fade as he just focused on Dawn's face…

 _'Wow… Was she always this pretty…?'_ Gary thought to himself, eyes finally finding their way back up to meet Dawn's gaze.

The whole scene was pretty awkward, two young adults just staring down each other after not even meeting for seven years, and even then they were more like acquaintances rather than friends. Now, nobody could deny that the attraction was there, it was written over both their faces.

"Y-you remember me?" Dawn inquired with a bit of surprise in her voice, she honestly didn't expect a guy like Gary to remember someone as 'plain and dull' as Dawn, or so she thought in her head.

"Oh crap… Er… Sorry you probably wouldn't remember me…Heh…" Gary stuttered awkwardly the confidence in his voice slowly draining rapidly.

Dawn quickly shook her hands in denial at the statement, "N-no! Of course I remember you, Gary…I just thought you wouldn't remember me is all…"

"Yeah that would be awkward if you remembered me but I didn't you." Gary said lightly hoping to lighten the mood.

"I guess it would have been…" Dawn sighed with a small smile as she rubbed her arm gently, looking towards the ground.

"N-not that I wouldn't remember you or anything! It's just I-ah… I'm sorry I can't speak properly today apparently." Gary chuckled to himself getting all tongue tied, it didn't happen often to him, in fact he could not even remember a time when he actually felt _nervous_ about talking to a girl. He usually was so smooth and the words always came out exactly as he wanted, but in this short conversation with Dawn, he couldn't even comprehend what he was going to say for some reason.

"Erm… So uh…What brings you to Sinnoh, in the middle of the woods?" Dawn bantered lightly, somewhat curious as to what exactly he was doing here.

"Oh yeah! I uh… My gramps-I mean Professor Oak said that there was something weird going on with the Sinnoh lakes and he told me to investigate anything out of the ordinary for his studies." Gary quickly finished not wanting to embarrass himself more than he already had.

"That seems awful tedious to come all the way from Kanto just to look at some water." Dawn gave herself a pity chuckle, "Have you found anything of interest yet?" She asked seeming like she was getting more comfortable now.

 _'Well I found you, and that's definitely something of interest…'_ Gary thought to himself tempted to say it aloud but he couldn't bring himself to do it in fear of scaring Dawn off. "Eh… Not really. I kinda only agreed to do it cause Sinnoh is on the way to another region that I've been planning on checking out for some time.

Dawn wondered what region he could possibly be talking about, but she didn't want to seem nosy so she kept her mouth shut as best she could. By the way he was talking it didn't seem like he was going to stay in Sinnoh long.

"So last I remember it… You were traveling with Ashy-boy and Brock right?" Gary turned up a small grin and was also curious on how her relations with Ash were.

"Oh um…They…We haven't traveled together for some time now…I haven't really seen them for years." Dawn sighed looking back down at her feet, clearly distressed about the topic being brought up again, just when she thought she could stop thinking about Ash the idea was forcefully shoved back in her head one way or another.

Gary quickly picked up on Dawn's sudden change of mood and desperately tried to change the subject.

"Er-S-So uh…What's been up with you lately, last I remember you were a coordinator, I've seen some of your performances on TV. You're really good, my gramps thinks so too."

"Oh! Uh… Yeah I still am a coordinator, I'm just on a little break right now…" She paused for a moment before continuing, "I'm not really all that great, it's a team effort with my Pokemon and me, can't have gotten to were I am today without that, I appreciate the compliments though." She cracked a smile, looking him straight into the eyes as she tilted her head a little to the left.

Gary felt his face light up a little and a buzz shivered throughout his body, ' _Arceus that was cute.'_

Dawn didn't know if she upset him or not, but the fact that he was just awkwardly standing there looking right back in her eyes made her feel somewhat uneasy, did she say something wrong?

Gary didn't notice Dawn's inner turmoil as he just kept looking at her as much as time permitted, he noticed when she tilted her head back up straight and how her gorgeous blue hair seemed to flitter back elegantly back onto her perfect face… Geez, he really was a mess right now, his thoughts wouldn't even let him think of the right things to say as he normally would.

Another awkward silence ensued the forest, the only sounds heard were the faint chirps of some Starly in the distance, and the gentle bits of breeze causing a few stray leaves to gust up and about.

"So! I guess I should let you get back to your thing Gary, I don't want to hold you up or anything…Sorry about bumping into you again." Dawn cracked out a smile as she looked like she was getting ready to leave.

Gary couldn't take it anymore, her smile made his insides jittery, he wondered if it was even possible to be _this_ physically attracted to someone. There would be no way he could go without seeing her again before he left on his trip, he had to at least try and spit out something to see her again.

"I-youwant…see again?" He murmured out pitifully and immediately felt his cheeks darken red with embarrassment at the incomprehensibility of the sentence he just uttered.

Dawn put her finger up to her mouth and popped out her hip as she started at him in confusion. "Is that some kind of code language or something, sorry to say I don't speak it."

"I-um…What I meant to say was…Erm-I-I'm gonna be in this area for a few more days and I was thinking it m-might be nice to catch up or something." Gary's face was now completely beet red and Dawn couldn't help but smile at his nervousness, what was he so nervous about anyways she wondered.

"Yeah sure! That sounds like fun, I haven't been doing anything these past few weeks anyways."  
Dawn smiled back at him. ' _Yeah except crying my eyes out about my failed love life with Ash.'_ Her mind quickly jabbed in the thought to erase that smile as best it could.

Gary's face lit up and he had this huge smile on his face when Dawn agreed, he scratched the back of his head and ruffled a bit of his messy spikes. "G-great, I guess I'll see you around then?" He was almost humming with bliss.

"Well you should probably get my number otherwise it will be difficult to find me, hehe." She chuckled as she pulled out her cell phone she carried with her.

"Oh shiiiierr-I mean yeah, yes that would probably be best." Gary chuckled as he tripped over his words once again. Quickly pulling out his phone and copying her number as thorough as possible, he would probably never forgive himself if he copied it wrong and wouldn't be able to see her again.

"Alright looks like we are all set then, I better get home before it gets too dark." Dawn said as she looked up towards the sky, the sunset already almost completely gone and the sky beggining to turn a light shade of purple.

"I-I can walk you home-If you want that is I don't want t-"

"I'd love for you to walk with me, that is if _you_ want to." Dawn began to get a little bit more playful as she noticed Gary tended to mix up his words a lot, she was still oblivious to his obvious attraction towards her though.

Gary just nodded his head up and down several times before taking his place next to Dawn at her side. Obviously he didn't know where she lived so he would just be following her for the time being.

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Dawn felt a lot safer now that Gary was by her side walking home, that Ariados attack earlier really shook her up and she would hate running into some other random Pokemon at the brink of night.

The walk began in silence which was fine with her, Gary kept looking up and down at her and Dawn couldn't help but feel like something was wrong with her.

' _I wonder why he keeps looking at me…? Is there something on my head or…?'_

Dawn scratched the top of her head, she didn't feel anything and it almost felt strange to her. She used to always go around with her hat everywhere so it was weird that she actually felt hair when she touched her head.

"So is Twinleaf town nice…?" Gary uttered randomly to break the silence of the walk. He instantly regretted his poor word choice and hoped Dawn would not notice.

Dawn looked at him as she continued walking and took her hand off her head as she answered, "Twinleaf town? It's kinda… boring?" She giggled softly, "I mean, it has a nice charm to it and all but after traveling around all of Sinnoh, Johto and Hoenn it really is just a small little town." She finished.

"Ha, yeah. I grew up in a small town too so I know that feeling, I just wanted to get out and explore the world as soon as I could." Gary smiled as he looked up at the sky remembering his younger days.

"Yeah…" Dawn sighed as she began looking up at the sky as well, continuing to walk.

The sky was littered with hundreds of stars which illuminated the deep purple it was beggining to turn as the sun slowly faded out of sight.

Dawn began thinking to herself, _'Maybe it is time I go on another adventure…'_ She smiled in hope that maybe going on another life changing journey would give her some solace in her sadness.

The walk was continued with other bits of light conversation, and for the first time in months Dawn's mind was finally off of Ash. She began to talk more and open herself as the walk progressed until finally they reached the door to Dawn's house.

Gary stood a ways from the door as Dawn began to head towards it. He watched as she grabbed the knob.

Dawn turned around before opening the door and spoke, "Thanks for walking me all the way home, I'm sorry I must have got you _way_ off track with this little detour."

Gary shook his head and smiled, "Nah, It was my pleasure. It was pretty nice just to relax and just take a walk y'know? Don't really do it that often."

"It's nice to just enjoy the little things sometimes." Dawn continued off his thoughts.

"So uh… I guess I'll call you tomorrow or something…?" He mumbled, his hands going into his pockets as he looked towards the floor.

"Yeah, sounds good to me." Dawn replied.

"Alright, I guess I'll see ya round then, Dawn." Gary concluded as he gave her a two fingered salute as a goodbye.

Dawn cracked a genuine smile, as she waved back and opened the door to her house.

Once she stepped in, she rested her back on the door, pulling out her phone and staring at the new number she put in today. She sighed out as with a smile on her face.

A smile that felt real… A smile made by someone else that she never would have expected.

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 **Gotta love those cheesy endings, next chapter will introduce some more characters that we all know and love. See ya soon ^u^!**


	3. Chapter 3- Chatty

**(A/N):I'm back pretty close in updates this time! I probably won't get to update for a little bit since I will be out of the country for several weeks, but I'll likely continue writing at night and if I have chance to connect to wifi I may end up doing that, who knows? Just stay tuned and hopefully the next update will be soon enough.**

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Dawn awoke the next morning to find herself still sleeping in the same clothes she wore yesterday for her run, she must have been tired because she could barely recall what even happened.

In her bed she sat up and yawned, not realizing that Piplup was asleep on the foot of her bed she accidentally knocks him up a bit with her foot. However, he is in too deep of a slumber to even notice as he continues snoring softly.

Dawn sighs with a smile as she grabs her phone, she then remembers the events that happened yesterday and her little encounter with Gary in the woods. It was strange, a feeling of 'happiness' was almost evident as she recalled those short memories of yesterday. She wondered if Gary would call her today… Not that she would be devastated if he didn't, but it would be _nice_ to spend some time with old friends is all.

At that thought Dawn's phone began ringing, she wondered if it was Gary calling, it would be ironic if that was the case when she was just thinking of this moment.

Quickly picking it up, not realizing she was excited, she quickly answered, "Hello?"

"Oh, hi Dawn!" A voice that sounded female spoke through the phone, obviously not Gary much to Dawn's dismay, although she didn't realize she was that upset.

"Er… Hi? Who is this?"

"What?! You didn't add me on your phone? Haha, classic Dawn move." The voice sounded peppy and Dawn immediately recognized the voice as May. Through the years, her and Dawn have maintained a great friendship from long distance and Dawn was actually quite happy to receive a call from her old friend.

"What? I _do_ have you added on my phone though?" Dawn looked a bit concerned as she let out a light laugh.

"Haha no you- oh wait…I changed my number so of course you don't have me added, bwhahaah!" May laughed uncontrollably through the phone, she was such a ball of energy, through the years she was almost up to the peppiness of people like Barry. Dawn just rolled her eyes as May continued.

"Ahaha… Ah…Well uh yeah, I didn't just call you just to laugh. I wanted to let you know that I received a call from someone asking if both you and I could travel to the Alola region in a few days to perform for like this Alolan festival or something, it sounded _really_ cool and I hope you will say yes when I ask you! Oh wait… I just did, haha."

Dawn paused for a moment, confused. "Wait, May. Who exactly is this _important_ person?"

"Well they refer to her as _Kahuna Olivia,_ in the Alola region."

Dawn nearly fainted, _the_ Kahuna Olivia wanted her to go to the Alola region?! This was almost a dream come true for Dawn, Olivia was an amazing trainer and Dawn has always admired her work, not to mention her amazing jewelry store Dawn would just _kill_ to visit.

"I-I uh… Oh my god May, how can I-I don't know if I'm even good enough to perform at something like that!"

"Nonsense! Olivia told me she was a big fan of your work and she said it would really be something special if you decided to come, I mean you are like a famous coordinator, give yourself some credit girl." May replied enthusiastically.

This was all moving so fast for Dawn, she was actually seriously considering this, after months of depression maybe a vacation would do her good. Then she realized something.

Ash would be there.

She didn't know if she could handle seeing him in her current state, but the odds of running into him on an entire region were slim. She would have to seriously consider this before deciding straight away.

"Uh… I have to think about this for a bit May, can I call you back?"

"Sure! Just let me know asap, the boat will be in Sinnoh in a few days and you can hop on then if you decide to come along, which I reaaaaalllly think you should Dawn." May pleaded through the phone sounding desperate in a joking way.

"Ugh, are you making that face you always make?" Dawn scoffed with a smile at her phone.

"W-what face?!" May sounded taken aback.

"That annoying face you always make when you want something, your lips all puffy and your eyes get all watery, trust me it's not as cute as you think it is." Dawn began to tease.

"Oh shut up Dawn! You better call me back _tonight_ saying you are coming on this freaking boat!" May screamed into the phone, causing some people to start telling her to be quiet on the other line.

"Haha… Ok ok, I'll let you know. Talk to you later." Dawn sighed elated.

"Ciaoooooo!" May rang as the phone hung up silently.

Dawn shut off her phone and went into the bathroom to finally get ready for the day. Putting her phone on top of her dresser as she did.

* * *

"I told you Misty, I can't just call her _this_ early! What if she thinks I'm like obsessing over trying to talk to her!" Gary clutched his phone tightly, eagerly awaiting an answer from his friend Misty on the other line.

"Well that's _exactly_ what you are doing." Misty replied with extreme sarcasm and sass in her voice.

"S-shut up and help me figure this out will ya! I've never wanted to make a better impression on anyone before…" Gary blushed at the sound of his own words, he usually wasn't the type to get all sappy about his 'feelings' or whatever. He could really open up around Misty as over the years they have become best friends and often confided in each other about their issues. Much like Dawn and May's relationship.

"Aww… I can _feel_ you blushing all the way from Kanto." Misty sang teasingly.

Gary just scoffed in his phone and pouted his face annoyed as Misty spoke once more.

"Ok ok ok, Gary I'll help you… geez." She paused a second before speaking again. "So this 'Dawn' chick, she must be a real _catch_ to make _the_ Gary Oak swoon like a Butterfree in a field of flowers." Misty gave herself a chuckle through the phone.

"You wouldn't believe… She's the most beautiful woman I've ever seen… She-she-"

"Alright bucko, I didn't ask for all the deets, _yet._ " Misty chuckled again through the phone interrupting Gary's train of thought.

"Ah-er right…" Gary stammered, blushing all the while as he got carried away in his thoughts of Dawn once again. It had been less than a day and already she was occupying a lot of his thoughts.

"Ok, so here is what you are going to do. You're gonna play it cool, and you are going to wait for a few more hours before making a _single_ call to her, no more, no less."

"Wha-uh but Misty! What if she doesn't answer her phone on that one single call?!"

"This is exactly why you need my help Gary, you obviously don't understand women at all, despite being such a ' _playboy_ '." She coughed subtly as she continued.

"If she is actually interested in spending time getting to know you, believe me she will pick up. Don't force it on her if she doesn't answer, that's basically a girl's way of saying 'no thanks'." Misty concluded sounding pretty proud of herself at the end of the statement.

Gary wasn't sure he believed in Misty's tactics, surely not all women thought exactly alike, but at this point he was desperate to make sure this worked. So he would do it, he would make one call and pray to Arceus that she picked up.

* * *

Dawn lounged around on the couch, sitting next to her mother watching the television. Johanna was elated to see that Dawn was finally out of her room and willing to 'attempt' to socialize with another human being at the least. Still, she wondered what could have caused her rapid change in mood, it was the motherly instinct in her that always caused her to worry despite Dawn always saying that she need not to.

While sitting, Dawn finally spoke.

"So I uh… Got a call from May today."

Johanna sat up, clearly interested. "Oh? What did she have to say?"

"She er… Wanted me to go with her to Alola, apparently I was asked to perform in some festival they have going on there but I'm not sure if it's a good idea-"

"Oh my goodness Dawn! That's so wonderful!" Johanna clapped her hands with joy as she beamed at Dawn.

"We'll have to start getting your things packed now! When do you leave?! Oh goodness, I'll pack some snacks!" Johanna excitedly got up from the couch and ran into the kitchen.

"Wait! Mom! I didn't say I was going to go yettttt….ughhhh.." Dawn groaned as she slumped back into the couch. As she did, her phone began buzzing signifying someone was calling. Dawn didn't even notice really as she began pouting that her mother jumped to some conclusion so rapidly, frankly she was a little angry but she knew her mother just wanted the best for her in the end.

Dawn didn't even realize the phone stopped buzzing as she slumped back in her chair and continued watching the television.

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 **(A/N):Ha... I loved writing my interpretation of what May and Misty would act like aged up a bit. Just fun to mess around with different types of personalites and such. See ya next time!**


	4. Chapter 4- Is this a date?

**(A/N): I'm backkkkk! I just want to take a second to thank all my reviews, follows and favorites I've gotten, you guys are awesome! I'll be honest when I say this chapter is short, it was partly due to my own laziness and the fact that I'm still extremely jet-lagged from my trip. I didn't want to leave you guys with nothing for so long, so I put together the most I could and made it into sort of a 'filler' almost. So yeah, sorry about the shortness but I'll try my best to make the next chapter a bit longer but it may take a bit longer with the snail pace I write at.  
**

* * *

Gary gripped the phone tightly in his hands, with his grip it was a miracle that it didn't smash into pieces right then and there. His hands were sweating with nervous anxiety brimming the air, eagerly he sat hoping she would pick up the phone when he called the first time following Misty's advice, after all it was late enough in the afternoon that she would be up hopefully.

He sat perched up on the window sill of the Pokemon Center in Sandgem town he was staying in. The bright light from the sun glimmering and illuminating his eager face as he quickly began warming himself up to talk to Dawn, even if it was over phone he still wanted to make himself look presentable. There was no way he was going back to the disaster of yesterday, he made a total fool of himself. He wasn't his typical smooth and relaxed type of personality that just made the ladies melt all over him, he was a stuttering mess and it reminded him of how Ash used to act when they were younger, almost pathetic. He held no ill-feelings for Ash now, but that rivalry spirit never truly died down after all the time that's passed.

As he was mentally preparing himself, he realized that the phone had gone to voicemail, his phone wasn't on speaker but he could still hear her voice even though it was set down beside his leg.

"This is Dawn Berlitz, I'm not here at the moment, obviously." The phone projected her soft, pure voice with a hint of elation hidden within, Gary grinned at her sarcastic tone as it continued.

"If you need to talk with me, call me again soon, I don't really check voice mail honestly and I'm not the type that cares if you spam me with calls or that, because I totally do that to every-oh wait this is going on too long ha, yeah…so I better wrap this up before the thing en-" The message concluded with a beep before Dawn could even finish earning a small chuckle from Gary as he concluded he wasn't about to leave a message after what he just heard. How cute she sounded when she making that message, how wry and witty she seemed, he really could not wait to see more of that if he were to ever see her again, which he so desperately wanted to do.

He wasn't about to let the fact that she didn't answer her first call bring him down, he would wait a bit and then call again, and again, until hopefully she would answer. He may be acting a bit adamantly but then again he is Gary Oak, and Gary Oak takes what he wants.

* * *

Dawn finally got up off the couch after hours of just blankly staring at contest re-runs she's observed countless times in the past already. Pacing around the house bored, she decides to check her phone to see if anyone had called her yet, and just as she had hoped she did get a call, a missed one from Gary. She decided it was fine for her to call him back, in case he didn't call back so she did just that, awkwardly fixing her hair and trying to appear vivacious and pretty even though they couldn't see each other, similar to what Gary did earlier ironically.

* * *

Gary felt his heart pounding loudly as his phone rung, he was not expecting Dawn to call _him_ back. Quickly rushing his hands through his spiked messy hair, which was even more wild in the mornings, his hand just caused it to bristle up even further than usual. Grasping the phone in his hand he hit the answer button and held it to his ear to listen.

He heard the faint breath on the other side of the line before she opened her mouth to speak.

"H-hey! Gary?" She questioned seeming a bit unsure.

"Oh, hey Dawn." Gary said smoothly with much more confidence.

"I was just wondering if you weren't doing anything right now… Or I mean later we could… I-mean I figured we should probably catch up or something since you said you weren't going to be here long." She sounded so nervous on the other line, Gary wanted nothing more than to just go over there and ease all her worries, he almost felt bad she was feeling that way about the call.

She opened her mouth to continue speaking, "You don't have to though, I don't want to seem lik-"

"I would be happy to meet up with you, Dawn." He emphasized her name unintentionally.

"I-uh… Ok! How about later tonight, we can go to like a restaurant or something, unless you don't want to…"

Gary sighed a little, was Dawn always so doubtful of herself? He thought to himself as he spoke clearly.

"Yeah, sure. Want me to come over to Twinleaf town in a few hours?"

"Ah-uh." She stammered, "I think it would be better for me to just meet you in Sandgem town, Twinleaf town has hardly anything to see really."

"Alright, sounds like a plan. I'll see you in a bit then." Gary smirked through the phone as he heard Dawn shuffle a little.

"Y-yeah… Bye for now." She sounded almost whispering, her voice sounding empty with almost 'remorse', but Gary detected a bit of hope from the back of it all, something happened to Dawn, and Gary was going to find out on this 'date' they had.

Yes, he was going to call it a date, and if it isn't, he was sure as hell going to make Dawn wish it was.

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 **(A/N): See you all next time! Ciao ;3!**


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